NOW, MHI LITHIUM ALUMINUM HYDRIDE FOR NITROGEN GROUP REDUCTIONS!
a new application development offering many important advantages Of major interest, LAH will reduce these groups in standard equipment at room temperature and a t atmospheric pressure. This cuts costly setups by eliminating the need for high-pressure hydrogénation equipment. Secondly, LAH provides bigger, more profitable product yields. A powerful, as well as versatile agent, L A H reductions are fast. Equally important, LAH is easy and safe to handle using standard techniques. The following are typical of many nitrogen-group reductions which can be carried out successfully with LAH: FUNCTIONAL GROUP
FORMULA
PRODUCT
FORMULA
j—9 = 0 ι—CH| Imide R NH Amine R NH I—C = 0 '—CH2 The reduction of imides to cyclic amines is analagous to that of amides and lactams consuming a total of one mole of LAH per mole of imide for the reduction of two carbonyl groups to methylenes. Amine -fAlcohol
RNHCOOR'
Carbamate
RNHCH3 + ROH
Carbamic esters undergo reduction cleavage to produce mixtures of N-methylamines and alcohols. Oxime R2C = N0H Amine R2CHNH2 The reduction of oximes forms the primary amines, in general, free from by-products. However, it is frequently necessary to employ forcing conditions to increase the rate of reduction. Hydroxylamine RNHOH Amine RNH2 Mono and di-N-substituted hydroxylamines react with LAH to furnish primary and secondary amines, respec tively. The oxygen atom in tri-substituted amineoxides is eliminated by the hydride and tertiary amines are obtained. Azide RN 3 Amine RNH2 The reduction of aliphatic and aromatic azides yields primary amines. The best solvent tetrahydrofuran*
for LAH nitrogen-group
reductions
is
TECHNICAL BULLETIN AVAILABLE. A copy will be sent to you immediately upon request. There is no obligation, of course. PIONEERS
IN H Y D R O G E N
Metal Hydrides 6 3 0 CONGRESS
14
C&EN
JUNE
3 0,
1958
COMPOUNDS
Incorporated
ST., B E V E R L Y , M A S S .
